So when do you stop upgrading the OS version on older hardware? And why?
Do you ever feel it's worth being "left behind" on upgrades in order to maintain your current functionality?
Or do you push the upgrades until the hardware is no longer compatible?

For instance, I am sitting at a Early 2008 iMac running OS 10.6.8. I suppose I could bring it up a few more versions of OS X, but I'm faced with having to update/replace/lose some of my existing software (Quicken 2006, Office 2004, pre-12 versions of FileMaker Pro, etc.). If I were to upgrade this machine, I'd probably want to do a clean install. Without physical media for all my software, this might be a huge risk (but I digress).

I have a 2011 MacBook Pro that I could take to 10.12. I'd lose a couple of older programs I use occasionally for backwards compatibility which I could maintain on the older iMac. But how far out can you go before performance losses outstrip functionality gains?

I am lucky that these days, there are no apps I have that won't work on the later OS's from Apple. However, IF* I had applications that were dependent on older OS and wanted to move forward, I might consider multi-boot options depending on how frequently I use those applications. Today, for me, I have a virtual of Win 7 and Win 10 because I use a couple of apps that only run under Windows.

So when do you stop upgrading the OS version on older hardware? And why?
Do you ever feel it's worth being "left behind" on upgrades in order to maintain your current functionality?
Or do you push the upgrades until the hardware is no longer compatible?

For instance, I am sitting at a Early 2008 iMac running OS 10.6.8. I suppose I could bring it up a few more versions of OS X, but I'm faced with having to update/replace/lose some of my existing software (Quicken 2006, Office 2004, pre-12 versions of FileMaker Pro, etc.). If I were to upgrade this machine, I'd probably want to do a clean install. Without physical media for all my software, this might be a huge risk (but I digress).

I have a 2011 MacBook Pro that I could take to 10.12. I'd lose a couple of older programs I use occasionally for backwards compatibility which I could maintain on the older iMac. But how far out can you go before performance losses outstrip functionality gains?

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Been a Mac user for a long time: as soon as you have an SSD in your machine, update it to it's max. You'll need a clean install every two major updates or so, but I haven't had any performance issues.

"Going forward", I would take that one no further than 10.8.5 (Mountain Lion).

Reason why:
From Mavericks (10.9) to the present, the Mac OS seems to be engineered to run best on computers with either an SSD or a fusion drive.
The OS will still run on Macs with platter-based hard drives, but from the viewpoint of the user, the experience may seem more like the OS is "walking" instead of "running".

I realize the perception of speed is an individual thing and every users' experience will be different.

Again, I wouldn't take that one further than Mountain Lion.
And be happy with that!

OP: My experience with old 2007 iMac with hard drive and slightly slower than your Mac shows that 10.9 is is slightly slower than 10.8. Newer OS versions are even slower. I don't mean unusable but 10.8 or 10.9 would be latest OS I would install on a older Mac with a hard drive. On a SSD difference isn't as noticeable but newer OS is still slower.

I would either keep 10.6.8 or install 10.8-10.9. Newer OS versions are likely clearly slower.

I have a 2007 iMac and I am upgrading the CPU to a T9300 from the X7900 that I put in it a few years ago. The T9300 will allow for macOS Sierra to be installed.
I already updated the wifi and Bluetooth to a newer combo card so it now has 802.11ac and Bluetooth 4.0 and supports handoff and continuity with the clipboard.
A few other upgrades are a ssd drive and I removed the SuperDrive and installed a caddy that accepts a 2.5" hard drive. And 6 GB of ram
Right now it's on El Capitan and runs great

This question isn't really about older hardware. The real issue here is "How far do you take OS upgrades when they might be incompatible with some of your current applications?" Forget what hardware you happen to have, focus on that, and the answer will probably jump right out at you.

This question isn't really about older hardware. The real issue here is "How far do you take OS upgrades when they might be incompatible with some of your current applications?" Forget what hardware you happen to have, focus on that, and the answer will probably jump right out at you.

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Sorry I haven't been back here in a while.

I think you did cut through the clutter in my question. I think leaving it at 10.6.8 might be the best option. However, I do need to do a clean install on it, and making sure I have access to all the old software is going to be critical before I get started. (This iMac is really grinding at times.)

Quicken hasn't added any usable functionality since 2000. (I actually liked 2000 a lot better than 2006!) Office hasn't added any ground breaking, "must have" features in years. And reverse compatibility is only a minor issue.

FileMaker Pro has been really problematic for me. I use a lot of different versions for different clients. It's expensive to upgrade. And FMP seems intent on moving to server based systems, limiting reverse compatibility, pushing OS requirements, and removing functionality that drew me to it in the first place.

It's the classic question of whether using older software is more important than any new functionality you may get from the OS upgrade. I've always been a "latest OS" person, going back to the days of MS DOS, so my answer would be, "Do it," but this isn't a one-size-fits-all world.

I prefer the gradual learning curve that comes with staying up-to-date on the OS and apps than skipping multiple generations of upgrades and having to deal with all the accumulated changes once circumstances force an upgrade. But that applies more to primary machines than secondary machines. If you already have a newer OS on a newer machine, then you've dealt with the learning curve/software update issues already, it's just a matter of whether you want/need to have all your machines on the same page.

Meantime, in the case of Snow Leopard... regardless of how good it's been, more and more secure websites are likely to refuse to support a browser running on it (and one of these days, major plug-ins may stop supporting it). If you want to sync/restore an iPhone running iOS 10, you'll have to upgrade OS X to at least 10.9.5 in order to run a compatible version of iTunes. You'll run into newer apps that will not support it. Maybe one or more of these factors are important to you, maybe not.

If it's your only Mac, these circumstances may force you to upgrade, but if you have another Mac capable of living in the "modern world," maybe you can leave the old Mac as-is.

I have an early 2008 iMac running El Capitan. After I got my Late 2013 iMac, it had been my OS X beta test bed (of course, I couldn't run the Sierra betas) - betas on the older machine, final-releases-only on my primary machine. Now, it's just one of several Macs around the house, a convenience for when I want to work/play in its location. Since I can access all my iCloud data, Apple Music, etc., it's far more useful to me on El Capitan than if it was running something significantly older, like Snow Leopard, Lion, or Mountain Lion.

That old Mac's performance isn't great, but it's no worse under El Capitan than it was under Mavericks - EtreCheck has been very helpful in that regard. The DVD drive quit years ago. I see no point to replacing it; the only thing I'd use it for is booting OS X Utilities from the Snow Leopard install disk. (Since the machine doesn't support Internet Recovery, I have a bootable El Capitan installer on a thumb drive.) It still has its original spinning hard drive, which I suspect won't last much longer. While I'd find the process of replacing it with an SSD to be educational (and beneficial to performance), I'm not sure I want to spend even $100 on the machine.

So when do you stop upgrading the OS version on older hardware? And why?

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Not being flippant here, but my answer is when I buy a new Mac. I kept an old Mini on SL until buying a new one after El Cap came out. I could only take the old Mini to Lion, so it wasn't worth it. Just after making the change, I decided to wipe the old Mini. It refused to boot! (Phew! Talk about in the nick of time!) I disposed of it with the SL disc still stuck inside. But, now that OS upgrades are free, this isn't an issue for me. I could afford to buy the upgrades, didn't want to.

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